Holiday houses in St. Johns County

Enchanted Oaks Estate-Weddings -Carriage House

1920 Carriage House on lush private estate. Renovated and charming! Situated on secluded, majestic 6 acre riverfront property on the St. John’s River. Enjoy park like grounds filled with azaleas, ancient oak and hickory trees, dripping in Spanish moss. Sit back and watch and listen to hawks and bald eagles overhead! Wake up to a magical sunrise each day! See the manatees lazily grazing! Bass Pro Shop shot their Spring Catalogue here! Owners home is on the property and they are always available

Family · Value · TV

Private oasis, heated pool, exceeds expectations

Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

Value · Family · Checkout

Walk Historic Downtown! “Blue Heaven”

Stunningly renovated cottage combines modern amenities with vintage charm... * 2 master suites with queen beds * Quiet neighborhood walking distance to explore The Nation's Oldest City * Clawfoot tubs inside and out (along with showers, of course!) * Big screened-in porch with hanging daybed * Off-street paved parking * Fully fenced backyard, Weber grill, gas fire pit * Fast Wi-Fi and Smart TV * 2 blocks to Fish Camp, Ice Plant, LaNuvelle, trolley stop * 10 minute walk to central downtown

Family · Location · TV

Historic Couples Retreat | 4 Unique Experiences

Escape to our 100-year-old historic home in Uptown St. Augustine, thoughtfully renovated for one couple seeking a unique getaway. Relax in the cozy primary suite and discover three beautifully themed rooms designed to spark fun, connection, and unforgettable memories. Minutes from Historic Downtown, restaurants, shops, and attractions. Perfect for anniversaries, birthdays, honeymoons, and romantic escapes. Explore our other Hidden Honey Homes. Travel insurance recommended. 25+ to book.

Value · Family · Hospitality

Historic Home in Downtown St. Augustine

The Triay-Hall house is one of the oldest Spanish Colonial houses in St. Augustine. It was recently fully restored and offers two bedrooms and two bathrooms. One bedroom/bathroom downstairs and the primary bedroom and en-suite bathroom is upstairs along with the Kitchen. The private courtyard is a serene oasis away from the busy streets of St. Augustine. The location is in the heart of downtown and the house comes with dedicated parking. Walking distance to the shops and restaurants.

Location · Value · Quiet

St Augustine Entire Home, King Bed, Pet Friendly

Casita Luxe Retreat Near Historic St. Augustine – Pet-Friendly Haven! Discover this luxurious 3-bedroom, 2-bath retreat! Designed with a modern luxe aesthetic, it features custom wood paneling, a fully equipped kitchen with a chic island, and a king-size plush mattress. Enjoy the large, fenced yard, fire pit, outdoor shower, and fun family games. Pet-friendly, with Wi-Fi, smart TVs, and parking included this home offers comfort and style in an up-and-coming neighborhood. Book now!

Location · Family · Bathroom

The Waddle Inn

Peaceful modern farmhouse 2-bed, 1-bath private 2nd-floor suite on our 2-acre creekfront mini farm. Built in 2023, it offers high-quality linens, smart TVs, and Wi-Fi. Meet our two rescue draft horses, friendly chickens and curious turkey; guests are welcome to help feed treats. Enjoy pool, firepit and on-site kayak rentals on the creek to the St. Johns River. 30–35 minutes to beaches, NAS JAX, TPC Sawgrass and historic St. Augustine. Perfect for couples, families and remote work.

Value · Location · Kitchen

The Shire on 1 acre marshfront with dock and Spa

One of a kind 1930s historic home, newly renovated and transformed into a beautiful secluded getaway. new luxury finishes, while holding its traditional charm. No Events allowed. Rooftop deck, sunrise views of the Atlantic ocean, Downtown, and sunsets over the river. The new dock with covered roof hosts a national geographic like eco system. It’s short walk to the beach and 3 miles to downtown St George street. Follow along @carcabaroad for weekly content of the home.

Value · Family · Getting around

Lagares

Escape to our beautiful private lake retreat! Enjoy fishing right from the property, relax in the jacuzzi, cool off in the pool, and create unforgettable memories with family and friends. Located just 30 minutes from Florida’s beautiful beaches and historic St. Augustine, our home offers the perfect balance of peaceful nature and nearby attractions. Spacious, comfortable, and fully equipped for the perfect getaway.

Family · Location · Amenities

MARE Florida Direct Beachfront St Augustine/JAXNEW

Beachy eclectic shabby chic decor Awesome patio overlooking the beach Amazing cabana with dining table and Adirondack chairs. Chaise sun lounges Beach chairs, beach towels and umbrella for the beach Super close to night of lights downtown St Augustine that offers great restaurants, shopping and night life Ask about our snowbird specials for monthly stays. Time to get Out of the cold and on the beach:)

Value · Location · Getting around

Cozy River Retreat w/ Hot Tub and an Amazing View

Cozy Waterfront Retreat with Stunning Sunsets Near Downtown St. Augustine Welcome to your perfect getaway! This fully renovated one-bedroom, one-bathroom home offers breathtaking water views and unforgettable sunsets. Perfect for honeymooners, anniversaries, or a quiet couples getaway where time slows down. Located just 20 minutes from the historic charm and vibrant culture of downtown St. Augustine.

Value · Location · Walkability

Modern Townhouse | Chef Kitchen | Near Beach & DT

Quiet, clean and genuinely well cared for. This townhouse sits in a peaceful St. Augustine neighborhood, 10 minutes from the beach and 15 from historic downtown. Coffee and snacks are waiting when you arrive. The kitchen has real counter space and full appliances. Two bedrooms, one with a queen bed and one with a bunk bed, plus 2.5 bathrooms and a patio to start your mornings right.

Location · Value · Bathroom